Asymmetric synthesis of homoallylic amines via 1,2-addition of Grignard reagent to aliphatic N-phosphonyl hemiaminal

Shuo Qiao, Suresh Pindi, Preston T. Spigener, Bo Jiang, Guigen Li

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

A general method for asymmetric synthesis of alkylated homoallylic amines was developed via a one-pot three-component reaction of easily available N-phosphonyl amides, aliphatic aldehydes, and allylic Grignard reagents. As anticipated the reaction proceeds through six-membered chelation controlled mechanism, allowing 1,2-nucleophilic addition to directly give chiral homoallylic amines with high yields and excellent diastereoselectivity.

Original languageEnglish
Pages (from-to)619-622
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number5
DOIs
StatePublished - Feb 3 2016

Keywords

  • 1,2-Nucleophilic addition
  • Alkylated homoallylic amines
  • Group-assisted-purification (GAP)
  • N-Phosphonyl amides
  • N-Phosphonyl imines

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